Agree about a lot of redundancy.
* Rather than two pocket pistols and a .357, how about just a snub-nose .38 like the S&W 642? Easy to shoot, concealable, and yet plenty capable for self defense. Plus, if you are out where there are snakes, then it is very handy with CCI shotshell rounds.
* The AR and AK are redundant. I would get either 2 AR15s, or one M1A (or Garand) and one AR15.
* The Tomcat .22 is redundant with the .38 or .32. Instead of that you could get a .22 conversion unit for your 1911, or a Ruger Mk III or Browning, etc. with a 4" - 6" barrel for lots of fun at the range.
Assuming you have the guns listed in your sig line I would recommend something like the following with an emphasis on self-defense and SGTF, with hunting as secondary.
* A battle carbine or rifle, preferably two. Two AR15s, one M1A or MA Garand, or one AR15 and one M1/M1A. These are for the worst case scenario, and long term riflemen skill building.
* Two pistols, preferably of the same caliber. If you already have the P99 and 1911 then just keep them as is. If you are starting clean I would get two of the same that can share mags, like a full size and compact. Caliber is really a personal choice, as the handgun is mainly be to get you away from the situation, or get you to a rifle or shotgun. No need for a full size revolver as long as you have the .45.
* One pocket handgun. If starting fresh then I think a pocket revolver is one of the handiest. Very reliable, can shoot the .38 round, and can shoot shotshells for snakes. Reasonably controllable and comfortable for anyone to shoot (both my daughters are decent shots with the S&W 642, although the shrouded hammer version may be better, the 638 Bodyguard?). No need for the .22 or .32 pocket pistols. The pocket revolver gives you a revolver and a pocket gun in one package.
* Pump shotgun, Mossberg 500 or Remington 870. The single shot is not much use for SD. Keep it for sport as you will not likely get much for selling it.
* A .22 of some sort. The rifle is probably more versatile for target practice, pest control, and small game hunting. If you want a second one then get a full size .22 pistol or revolver, but the tomcat really doesn't add anything to the mix.
The absolute minimum I believe is:
* One battle rifle or carbine
* One pump shotgun
* One pistol of 9mm or greater caliber
- a compact version can usually do everything you need: concealed carry, nightstand, hiking, etc.
* One .22 rifle.
After that, then getting seconds for the rifle/carbine and handgun are priority.
You sound like you're just now getting into guns and if so, you might be like me and totally change your preferences and sell your first few guns to get something totally different. If you buy the 9mm first, your fiancee might find that she likes that particular gun and doesn't want anything smaller. Or has she had a chance to fire .38s yet? 
